The company taking 75 “remotes” around the world for a year—for $27,000—has grown and come under criticism in its inaugural year. Is it an idea that can last?

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Those who are accepted into the Remote Year program must already have a job that will allow them to work remotely for 12 months.
Photo: Jovo Jovanovic

Geetika Agrawal arrived in Lima, Peru, at the beginning of May, to a new home, a new language, and a new national drink to sip on—pisco sour. She bought flowers and groceries, unpacked her 50-pound suitcase, organized her spices, and rolled out her yoga mat. She studied a map and a calendar of events for the next four weeks. She walked down the street and familiarized herself with the co-working space she’d head to each morning—a trendy office with a garden, small cafe, and a slide connecting the first and second floor.

This was the 12th time Agrawal completed the ritual this year, having already hit locales like Prague, Hanoi, and Santiago. From June 2015 to May 2016, she unpacked, settled in, and repacked for a new country every month. And once the year is up, she'll return to the her advertising job back in New York City.

The wanderlust that pervades our Instagram feeds and viral-stories-of-the-day seems totally at odds with the fact that hundreds of millions of vacation days go unused every year. Outside of the Internet, most of us have a hard time actually taking leave of the office. The plunge digital nomads take—quitting their jobs, becoming Insta-famous, living in a van—feels unrealistic for a lot of people. A company called Remote Year is offering an alternative to the 9-to-5 or drop-off-the-grid dichotomy. The sell: You can grow your career while living in a new city every month for a year. Applicants must already have a job that's okay with the idea of working remotely for a year. (Agrawal is a unique case among the group—her company is allowing her to take a year-long "sabbatical" for the trip, and she's running her own small business during her Remote Year. But she'll return to her regular job when the year is up.) If selected, participants pay a total of $27,000, and Remote Year handles all other logistics, including city-to-city travel plans, accommodations, and co-working spaces with 74 other professionals on the trip.

At first glance, it seems ludicrous to pay a price tag that’s very close to some people’s full salaries just to work in a new city each month. But after the $5,000 upfront deposit, it adds up to $2,000-a-month rent and a full year of travel with other young professionals. A growing number of people want in on that plan. Greg Caplan, the company's founder, and Heather Lee, communications director, shared via e-mail that they received about 50,000 applications for 2016-2017 programs, which will be Remote Year’s second round.

Agrawal started the year in a group of 75 professionals, ranging in age from 23 to 64 and comprising over 30 nationalities. (There’s another group of 75 "remoters," who followed the same itinerary a few months later.) No, they're not all from the tech space—well, about 50 are. There are also writers, consultants, small business owners, artists, even a lawyer. The company wants a diverse mix with the goal of fostering exchange of knowledge and experience.

For Agrawal, it would be far cheaper to go it alone, staying in hostels and bed-and-breakfasts. But “the idea of doing it alone was daunting,” she says. “I was mentally ready to travel for a year, I just wanted to focus on my work and have someone else worry about the logistics. And the experience in a city is significantly better living in [your own] apartments. Having a kitchen, a couch to sit on, and a coffee table make all the difference.”

The monthly stability and the opportunity to explore without travel hassle are the biggest draws for many. Remotes are people who enjoy their work, crave the road—or aisle seat—and love meeting professionals across industries in places like Kyoto, Japan. As Lee points out, “Whether at home or away, the monthly expenses of living in a metropolitan city are not too far off [the expense] of traveling the world and keeping your paycheck.” And day-to-day for Agrawal, she sees the benefit. “We basically work during the day and explore the city every night.” It’s the adult table for study abroad students—on steroids.

The co-working space in Lima.Photo: Courtesy of Geetika Agrawal

Some of the group during their Hanoi motorcycle trip.Photo: Courtesy of Geetika Agrawal

Agrawal's apartment in Lima. Photo: Courtesy of Geetika Agrawal

Remote Year is also selling something the intentional travel community values above all else: experiences. With a network of colleagues and built in connections with locals via coworking spaces, there’s little adjustment time and rapid immersion. In each city, the company organizes outings and cultural activities. A highlight for Agrawal was a weekend motorcycle trip to an overnight homestay in Mai Chau Valley in Vietnam.

As the startup’s first year comes to a close, it’s important to point out the hiccups Caplan and his team encountered in their first year. With some questionable accommodations in a few cities, like a bug-filled high-school dorm in Slovenia, and failure to uniformly implement policies like an early-exit fee, the first batch of travelers dwindled down to a 50 percent of its initial size, according to a recent article from Atlas Obscura. When asked to comment on the article, Lee said, “We are constantly learning from feedback we take from the participants and make frequent of changes to ensure everyone continues to have an amazing experience.”

We spoke to Joe Matta, a consultant out of New York City, as he wraps up his 12th month with Remote Year. He touts how the intangible aspects of the trip—selecting a diverse group of people and developing community through co-working spaces and group excursions—were well executed by the Remote Year staff. But in terms of the tangible aspects of the business, “They’ve had a few misses,” says Matta. “There’ve been some good and some bad months. They failed a little bit in the sense of accommodations, workspaces, and travel, but they are learning, and they’re good about responding to feedback.”

Despite their shortcomings, Caplan and company see more and more remotes wanting to capitalize on the opportunity to get up, go, and keep the job. They’re expanding their team to include a community manager and an operations manager to travel with each of the four programs launching concurrently this fall, for which the application period is currently open. Remote Year will also be adding local City Managers to their roster to ensure the most local experience possible for their travelers. Some of the cities on the next itinerary include Tel Aviv, Phnom Penh, and Medellín.

We asked Matta and Agrawal about the qualities that make a person a good fit for Remote Year. Matta said, “You have to be willing to make [Remote Year] your own experience… You have to be independent and strong-willed—a person that’s as happy in a large group as they are alone.” And as cliché as it may seem, despite having a built-in group of fellow travelers, remotes need to be adaptable self-starters, remembering that travel is one of life’s most unpredictable ventures.